US9162991, 14c

ID: ALA3960170

PubChem CID: 25023628

Max Phase: Preclinical

Molecular Formula: C15H10N4O4

Molecular Weight: 310.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1[N+](=O)[O-])[n+]1nn([O-])c2ccccc21

Standard InChI:  InChI=1S/C15H10N4O4/c20-15(10-9-11-5-1-2-6-12(11)19(22)23)17-13-7-3-4-8-14(13)18(21)16-17/h1-10H/b10-9+

Standard InChI Key:  FGIGZPJYRLBTLI-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -0.4916   -3.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8794   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520   -0.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8823   -2.5608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3509   -2.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538   -3.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8856   -4.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8857   -5.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -5.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8221   -4.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8221   -3.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2935   -1.6362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4684   -1.3923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4950   -0.7404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
  4 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23  2  1  0
 23 18  1  0
M  CHG  4   1  -1   4   1  15   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3960170

   (E)-3-(2-nitrophenyl)-1-(3-oxidobenzotriazol-3-ium-1-yl)prop-2-en-1-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 310.27

Molecular Weight (Monoisotopic): 310.0702

AlogP: 1.93

#Rotatable Bonds: 3

Polar Surface Area: 104.97

Molecular Species: ACID

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.80

CX Basic pKa: ┄

CX LogP: -0.17

CX LogD: -1.22

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.32

Np Likeness Score: -0.72

References

1.  (2015)  Cinnamoyl inhibitors of transglutaminase, 

Source

Source(1):

• BindingDB Database